347411-88-5Relevant articles and documents
Structural analysis of a family 101 glycoside hydrolase in complex with carbohydrates reveals insights into its mechanism
Gregg, Katie J.,Suits, Michael D. L.,Deng, Lehua,Vocadlo, David J.,Boraston, Alisdair B.
, p. 25657 - 25669 (2015)
O-Linked glycosylation is one of the most abundant posttranslational modifications of proteins. Within the secretory pathway of higher eukaryotes, the core of these glycans is frequently an N-acetylgalactosamine residue that is α-linked to serine or threo
Anti-cancer properties and catalytic oxidation of sulfides based on vanadium(V) complexes of unprotected sugar-based Schiff-base ligands
Mohammadnezhad, Gholamhossein,Mokhtari, Parisa
, (2022/01/26)
In this article, benzyl 2-deoxy-2-salicylideneamino-α-D-glucopyranoside (H2SalHGlc), a sugar-based Schiff-base ligand, as well as four of its derivatives including H2Sal5-BrGlc, H2Sal3,5-tBu/sup
Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity
Cheng, Wei-Chieh,You, Ting-Yun,Teo, Zhen-Zhuo,Sayyad, Ashik A.,Maharana, Jitendra,Guo, Chih-Wei,Liang, Pi-Hui,Lin, Chung-Shun,Meng, Fan-Chun
supporting information, p. 3836 - 3844 (2020/10/21)
A series of muramyl dipeptide (MDP) analogues with structural modifications at the C4 position of MurNAc and on the d-iso-glutamine (isoGln) residue of the peptide part were synthesized. The C4-diversification of MurNAc was conveniently achieved by using CuAAC click strategy to conjugate an azido muramyl dipeptide precursor with structurally diverse alkynes. d-Glutamic acid (Glu), replaced with isoGln, was applied for the structural diversity through esterification or amidation of the carboxylic acid. In total, 26 MDP analogues were synthesized and bio-evaluated for the study of human NOD2 stimulation activity in the innate immune response. Interestingly, MDP derivatives with an ester moiety are found to be more potent than reference compound MDP itself or MDP analogues containing an amide moiety. Among the varied lengths of the alkyl chain in ester derivatives, the MDP analogue bearing the d-glutamate dodecyl (C12) ester moiety showed the best NOD2 stimulation potency.
Targeting GNE Myopathy: A Dual Prodrug Approach for the Delivery of N-Acetylmannosamine 6-Phosphate
Morozzi, Chiara,Sedláková, Jana,Serpi, Michaela,Avigliano, Marialuce,Carbajo, Rosangela,Sandoval, Lucia,Valles-Ayoub, Yadira,Crutcher, Patrick,Thomas, Stephen,Pertusati, Fabrizio
, p. 8178 - 8193 (2019/09/10)
ProTides comprise an important class of prodrugs currently marketed and developed as antiviral and anticancer therapies. The ProTide technology employs phosphate masking groups capable of providing more favorable druglike properties and an intracellular activation mechanism for enzyme-mediated release of a nucleoside monophosphate. Herein, we describe the application of phosphoramidate chemistry to 1,3,4-O-acetylated N-acetylmannosamine (Ac3ManNAc) to deliver ManNAc-6-phosphate (ManNAc-6-P), a critical intermediate in sialic acid biosynthesis. Sialic acid deficiency is a hallmark of GNE myopathy, a rare congenital disorder of glycosylation (CDG) caused by mutations in GNE that limit the production of ManNAc-6-P. Synthetic methods were developed to provide a library of Ac3ManNAc-6-phosphoramidates that were evaluated in a series of studies for their potential as a treatment for GNE myopathy. Prodrug 12b showed rapid activation in a carboxylesterase (CPY) enzymatic assay and favorable ADME properties, while also being more effective than ManNAc at increasing sialic acid levels in GNE-deficient cell lines. These results provide a potential platform to address substrate deficiencies in GNE myopathy and other CDGs.
